trans-2-Aminocyclohexanecarboxylic acid → trans-2-[({4-[(2-Methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclohexanecarboxylic acid

HRID 736835Notes

Reaction equation

HRID 736835 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[C:8]([OH:10])=[O:9].Cl.[CH3:12][C:13]1[CH:22]=[C:21]([CH2:23][O:24][C:25]2[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=2)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1>>[CH3:12][C:13]1[CH:22]=[C:21]([CH2:23][O:24][C:25]2[CH:30]=[CH:29][C:28]([S:31]([NH:1][C@@H:2]3[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]3[C:8]([OH:10])=[O:9])(=[O:33])=[O:32])=[CH:27][CH:26]=2)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1

Participants

3

Reactant 2

HCID 2724640trans-2-Aminocyclohexanecarboxylic acidHCID 866078654-(2-Methylquinolin-4-ylmethoxy)benzenesulfonyl chloride hydrochloride

Product 1

HCID 68819595trans-2-[({4-[(2-Methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclohexanecarboxylic acidYield 25%

Procedure

According to the procedure of Example 10, Step 1, the reaction of 487 mg (3.4 mmol) of trans-2-amino-1-cyclohexanecarboxylic acid with 1.31 g of 4-(2-methyl-quinolin-4-ylmethoxy) -benzenesulfonyl chloride hydrochloride provided 382.7 mg of trans-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclohexanecarboxylic acid in 25% yield. MS: 455.1 (M+H)+

Sources & evidence

ORD record
ord-e4056dc2f14f4765ac4f42fd6bf41d38
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

Loading…